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Biomolecules question

2019 · 12 Jan · Shift 2 · Q8
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Biomolecules question

2019 · 12 Jan · Shift 2 · Q8

JEE MainChemistryBiomoleculesMCQ+4 / −1
The correct structure of histidine in a strongly acidic solution (pH = 2) is -
  1. A
    JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Biomolecules Question 143 English Option 1
  2. B
    JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Biomolecules Question 143 English Option 2
  3. C
    JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Biomolecules Question 143 English Option 3
  4. D
    JEE Main 2019 (Online) 12th January Evening Slot Chemistry - Biomolecules Question 143 English Option 4
View written solutionFree

Correct answer: B

  1. Identify the ionizable groups in histidine

    Histidine contains three important ionizable sites:

    • Carboxyl group: −COOH⇌−COO−+H+-COOH \rightleftharpoons -COO^- + H^+−COOH⇌−COO−+H+
    • Amino group: −NH3+⇌−NH2+H+-NH_3^+ \rightleftharpoons -NH_2 + H^+−NH3+​⇌−NH2​+H+
    • Imidazole side chain: can also be protonated
  2. Recall their approximate pKapK_apKa​ values

    For histidine, typical values are:

    • pKa(\ce−COOH)≈1.8pK_a(\ce{-COOH}) \approx 1.8pKa​(\ce−COOH)≈1.8
    • pKa(\ceimidazole)≈6.0pK_a(\ce{imidazole}) \approx 6.0pKa​(\ceimidazole)≈6.0
    • pKa(\ce−NH3+)≈9.2pK_a(\ce{-NH3+}) \approx 9.2pKa​(\ce−NH3+)≈9.2
  3. Analyze the situation at pH=2\mathbf{pH = 2}pH=2

    Rule:

    • If pH<pKa\text{pH} < pK_apH<pKa​, the group is predominantly protonated.
    • If pH>pKa\text{pH} > pK_apH>pKa​, the group is predominantly deprotonated.

    Now check each group:

    • Amino group: since 2≪9.22 \ll 9.22≪9.2, it remains protonated as \ce−NH3+\ce{-NH3+}\ce−NH3+.
    • Imidazole side chain: since 2≪6.02 \ll 6.02≪6.0, it is also protonated, carrying a positive charge.
    • Carboxyl group: since 222 is very close to 1.81.81.8, but in a strongly acidic medium it is taken predominantly as protonated \ce−COOH\ce{-COOH}\ce−COOH.
  4. Hence the overall structure at pH 2

    Histidine in strongly acidic solution will have:

    • \ce−NH3+\ce{-NH3+}\ce−NH3+ on the amino group
    • protonated imidazole ring (+1+1+1 charge on side chain)
    • \ce−COOH\ce{-COOH}\ce−COOH on the carboxyl group

    So the species is a dicationic form overall.

  5. Match with the correct option

    Therefore, the correct option must be the one showing:

    \ceH3N+−CH(CH2−imidazolium)−COOH\ce{H3N+ - CH(CH2-imidazolium) - COOH}\ceH3N+−CH(CH2−imidazolium)−COOH

    with the imidazole nitrogen protonated.

    This corresponds to Option B.

  6. Comparison with stored answer

    Stored correct answer = B

    Our derived answer = B

    So they agree.

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